Takeshita Street
This is the main shopping drag of Harajuku's fashion world. A narrow, pedestrian-only street, practically every nook and cranny is filled with things. You can expect this area to be pretty tourist heavy, and the added bonus of that is that some of the store clerks will speak some rudimentary English.
The first time I brought my fashion-forward brother here, he was in heaven. Male fashion stores and shoe stores abound, and fortunately for my brother, he fits into Japanese sizes. If you wear a larger size, shopping for clothes will be a challenge, especially in the more trendy shops. But don't be discouraged--it's always a good idea to ask. "Watashi no saizu ga arimasu ka?" means, "Do you have my size?" Let the fun commence from that.
One of my favorite stops along this street is the 100 yen shop, not far from the main entrance of the station on the left side of the road if you're heading away from the station. These shops were my lifeblood in Japan and are not to be compared to dollar stores in the states, where you get what you pay for. The 100 yen shops do carry standard one-use-before-it-breaks items, but they also carry a lot of great souvenir gifts and funky items for friends and family back home. If you've got room in your luggage, the housewares section usually has nice ceramics, Japanese-style plates and sake pitchers.
Note: You may see it referred to as Takeshita-dori. "Dori" simply means street in Japanese.
There are several spots along this street to grab a bite, but later on this tour Lotteria is a good fast-food chain pit stop. It's marked as a "minor" point along the guide route in the Omotesando area.